There's a fine line between "try a little harder" and "trying too hard." Wearing your pants nonchalantly tucked into your boots requires not only fastidious attention to detail, but also the right boots and pants. Madeline Weeks, the fashion director of GQ explains, "The proportion of the boot and the pants has to be right. You don’t want to the boots to be too short or too tall - say, four to six inches above the ankle, or up to eight if you’re really going to go there." Boots that are too short, or knee high, can be too costumey. Then, too, the pants need to be slim or even tight. SOURCE
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